The more I think about this... the more I want to take the body off the frame, pull the drive train, clean up the frame, swap in the trans and tc, fix the rust and paint the body while it's apart... so much to do and so little time and $ to do it.

Back to the original question, having done it both ways, stabbing the tranny has always been a chore whenever I've done one. Easiest is when the whole mess is on the floor, or when the body's off as I did on my 76 10 year project:-)

X2 on Ige's comment, Cherry picker works better than floor jack, although I've been successful with 2 floor jacks: one for the tranny and one for the lower part of the t-case. There's a bunch of tricks in this job, any way you work it, it's a bunch of work.

Sheesh - maybe we need a tranny swap/RMS party. Or at least a rotating pool of helpers for everyone. I've probably got the same job coming up, and so I assume that if I bother to pull the tranny, it would be a good time for a RMS job. That assumes I'm even capable of pulling and stabbing...